JP2007507511A5 - - Google Patents
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- Publication number
- JP2007507511A5 JP2007507511A5 JP2006534029A JP2006534029A JP2007507511A5 JP 2007507511 A5 JP2007507511 A5 JP 2007507511A5 JP 2006534029 A JP2006534029 A JP 2006534029A JP 2006534029 A JP2006534029 A JP 2006534029A JP 2007507511 A5 JP2007507511 A5 JP 2007507511A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- benzimidazole
- propoxy
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000004122 cyclic group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- -1 -OCH 2 Ph Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- PMSKRMBSAZKNAO-UHFFFAOYSA-N 6-tert-butyl-2-[2-methyl-4-[3-(2-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound CC1CNCCN1CCCOC(C=C1C)=CC=C1C1=NC2=CC(C(C)(C)C)=CC=C2N1 PMSKRMBSAZKNAO-UHFFFAOYSA-N 0.000 claims 2
- HOGIQAJOASEATP-UHFFFAOYSA-N 6-tert-butyl-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Cl HOGIQAJOASEATP-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- WFYUITPFJSNEQQ-UHFFFAOYSA-N 1-[2-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-5-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(C=2NC3=CC=C(F)C(C)=C3N=2)C(CN(C)C)=CC=1OCCCC1CCN(C)CC1 WFYUITPFJSNEQQ-UHFFFAOYSA-N 0.000 claims 1
- JMGPTTNPUMSBTQ-UHFFFAOYSA-N 1-[2-(6-chloro-4-methyl-1h-benzimidazol-2-yl)-5-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(C=2NC3=CC(Cl)=CC(C)=C3N=2)C(CN(C)C)=CC=1OCCCC1CCN(C)CC1 JMGPTTNPUMSBTQ-UHFFFAOYSA-N 0.000 claims 1
- AADBANJKFIORNE-UHFFFAOYSA-N 1-[3-[4-(6-tert-butyl-1h-benzimidazol-2-yl)-2-chlorophenoxy]propyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Cl AADBANJKFIORNE-UHFFFAOYSA-N 0.000 claims 1
- QSSIZKWOJDCWML-UHFFFAOYSA-N 2-[2-chloro-4-[2-methyl-3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C=1C=C(C=2NC3=CC=CC(C)=C3N=2)C(Cl)=CC=1OCC(C)CN1CCN(C)CC1 QSSIZKWOJDCWML-UHFFFAOYSA-N 0.000 claims 1
- CCHJDYXWLQLTHD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-3h-benzo[e]benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C(N1)=NC2=C1C=CC1=CC=CC=C21 CCHJDYXWLQLTHD-UHFFFAOYSA-N 0.000 claims 1
- ZBKOPZVHMTXXQH-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 ZBKOPZVHMTXXQH-UHFFFAOYSA-N 0.000 claims 1
- BYEFGIKEWXKOAC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 BYEFGIKEWXKOAC-UHFFFAOYSA-N 0.000 claims 1
- YPWPMKJVTQONQH-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 YPWPMKJVTQONQH-UHFFFAOYSA-N 0.000 claims 1
- RPIXQBZODSVPPC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 RPIXQBZODSVPPC-UHFFFAOYSA-N 0.000 claims 1
- JMQRDCNEFGNPAL-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 JMQRDCNEFGNPAL-UHFFFAOYSA-N 0.000 claims 1
- WMGUYQXCPREFOF-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 WMGUYQXCPREFOF-UHFFFAOYSA-N 0.000 claims 1
- PBYAQWILYFZYHC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC=CC=C2N1 PBYAQWILYFZYHC-UHFFFAOYSA-N 0.000 claims 1
- SKQKGGHCXLOMFJ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-3h-benzo[e]benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C(N1)=NC2=C1C=CC1=CC=CC=C21 SKQKGGHCXLOMFJ-UHFFFAOYSA-N 0.000 claims 1
- FKLHKZSFHAZKBD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 FKLHKZSFHAZKBD-UHFFFAOYSA-N 0.000 claims 1
- SIDSFFAOACXBRD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 SIDSFFAOACXBRD-UHFFFAOYSA-N 0.000 claims 1
- DIFIANIFCWCWIA-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 DIFIANIFCWCWIA-UHFFFAOYSA-N 0.000 claims 1
- NPYCKTMZMUAVJW-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-5-fluoro-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(F)=CC=C2N1 NPYCKTMZMUAVJW-UHFFFAOYSA-N 0.000 claims 1
- NYNGHPOORNFKGZ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(OC(F)(F)F)=CC=C2N1 NYNGHPOORNFKGZ-UHFFFAOYSA-N 0.000 claims 1
- KGTCKJNHHCXYEZ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(C(F)(F)F)=CC=C2N1 KGTCKJNHHCXYEZ-UHFFFAOYSA-N 0.000 claims 1
- FEMHOUCJHZSJJV-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(C)=CC=C2N1 FEMHOUCJHZSJJV-UHFFFAOYSA-N 0.000 claims 1
- KHADFEDGWBHJSK-UHFFFAOYSA-N 2-[2-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C=1C=C(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)C(OC)=CC=1OCCCN1CCN(C)CC1 KHADFEDGWBHJSK-UHFFFAOYSA-N 0.000 claims 1
- KBYGQHKVXVNPHA-UHFFFAOYSA-N 2-[3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=CC(C=2NC3=CC=CC=C3N=2)=C1 KBYGQHKVXVNPHA-UHFFFAOYSA-N 0.000 claims 1
- BHXFOAZKCRAEEO-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC1=CC=C(C=2NC3=CC=CC(C)=C3N=2)C=C1Cl BHXFOAZKCRAEEO-UHFFFAOYSA-N 0.000 claims 1
- UMNDIUWKZLKSRC-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1Cl UMNDIUWKZLKSRC-UHFFFAOYSA-N 0.000 claims 1
- ZJSRVCKWBKNRCM-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)C=C1Cl ZJSRVCKWBKNRCM-UHFFFAOYSA-N 0.000 claims 1
- PVHPABJTUPOEHL-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methoxy-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1C(C=C1Cl)=CC=C1OCCCN1CCN(C)CC1 PVHPABJTUPOEHL-UHFFFAOYSA-N 0.000 claims 1
- QMGSOQRJRHUXGG-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C=C3N=2)C=C1Cl QMGSOQRJRHUXGG-UHFFFAOYSA-N 0.000 claims 1
- GYWXPRKRKOTZFC-UHFFFAOYSA-N 2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1F GYWXPRKRKOTZFC-UHFFFAOYSA-N 0.000 claims 1
- PAHZWMXYPGJECS-UHFFFAOYSA-N 2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC(C)=C3N=2)C=C1F PAHZWMXYPGJECS-UHFFFAOYSA-N 0.000 claims 1
- FOWBFPKYEHZJDX-UHFFFAOYSA-N 2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C=C3N=2)C=C1F FOWBFPKYEHZJDX-UHFFFAOYSA-N 0.000 claims 1
- WXWJVMLNEFLGCC-UHFFFAOYSA-N 2-[3-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound COC1=CC(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)=CC=C1OCCCN1CCN(C)CC1 WXWJVMLNEFLGCC-UHFFFAOYSA-N 0.000 claims 1
- DOLJNIUPEWVSMY-UHFFFAOYSA-N 2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1C DOLJNIUPEWVSMY-UHFFFAOYSA-N 0.000 claims 1
- KUBYFJXKFPBGHW-UHFFFAOYSA-N 2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1 KUBYFJXKFPBGHW-UHFFFAOYSA-N 0.000 claims 1
- HIOACXJIFNRHFT-UHFFFAOYSA-N 4,5-dimethyl-2-[3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C(C)=CC=C3N=2)=C1 HIOACXJIFNRHFT-UHFFFAOYSA-N 0.000 claims 1
- XYCZNRPVEIXUGZ-UHFFFAOYSA-N 4,5-dimethyl-2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C(C)=C3N=2)C=C1C XYCZNRPVEIXUGZ-UHFFFAOYSA-N 0.000 claims 1
- CSEXYSDCKNILSQ-UHFFFAOYSA-N 4,6-dimethyl-2-[2-methyl-3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C=C(C)C=C3N=2)=C1C CSEXYSDCKNILSQ-UHFFFAOYSA-N 0.000 claims 1
- ZMUYSFLEOVTVQU-UHFFFAOYSA-N 4,6-dimethyl-2-[3-[4-(4-methyl-1,4-diazepan-1-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCCOC1=CC=CC(C=2NC3=CC(C)=CC(C)=C3N=2)=C1 ZMUYSFLEOVTVQU-UHFFFAOYSA-N 0.000 claims 1
- DBKCSJUURDYQKR-UHFFFAOYSA-N 4-[3-(6-tert-butyl-1h-benzimidazol-2-yl)phenoxy]-1-(4-methylpiperazin-1-yl)butan-1-one Chemical compound C1CN(C)CCN1C(=O)CCCOC1=CC=CC(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)=C1 DBKCSJUURDYQKR-UHFFFAOYSA-N 0.000 claims 1
- HEOOSKRYIMADSF-UHFFFAOYSA-N 4-[3-[4-(6-chloro-4-methyl-1h-benzimidazol-2-yl)-3-methylphenoxy]propyl]-1,4-diazepan-5-one Chemical compound C=1C=C(C=2NC3=CC(Cl)=CC(C)=C3N=2)C(C)=CC=1OCCCN1CCNCCC1=O HEOOSKRYIMADSF-UHFFFAOYSA-N 0.000 claims 1
- PXCXUOSJIMFZQQ-UHFFFAOYSA-N 4-[3-[4-(6-tert-butyl-1h-benzimidazol-2-yl)-3-methylphenoxy]propyl]-1-methyl-1,4-diazepan-5-one Chemical compound O=C1CCN(C)CCN1CCCOC(C=C1C)=CC=C1C1=NC2=CC(C(C)(C)C)=CC=C2N1 PXCXUOSJIMFZQQ-UHFFFAOYSA-N 0.000 claims 1
- LKAOLMAQJVBSHY-UHFFFAOYSA-N 4-chloro-2-[2-methyl-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1C)=CC=C1C1=NC2=C(Cl)C=CC=C2N1 LKAOLMAQJVBSHY-UHFFFAOYSA-N 0.000 claims 1
- RNBYJCBTCUPEML-UHFFFAOYSA-N 4-methyl-2-[3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C=CC=C3N=2)=C1 RNBYJCBTCUPEML-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- NBYUHYMOOAWKJK-UHFFFAOYSA-N 5,6-dichloro-2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(Cl)=C(Cl)C=C2N1 NBYUHYMOOAWKJK-UHFFFAOYSA-N 0.000 claims 1
- HUVLLIJCEAKWNB-UHFFFAOYSA-N 5,6-dichloro-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(Cl)=C(Cl)C=C3N=2)C=C1Cl HUVLLIJCEAKWNB-UHFFFAOYSA-N 0.000 claims 1
- YVBUIDRPKJTUJO-UHFFFAOYSA-N 5,6-difluoro-2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(F)C=C3N=2)C=C1F YVBUIDRPKJTUJO-UHFFFAOYSA-N 0.000 claims 1
- JYUNHIWFSACXRN-UHFFFAOYSA-N 5,6-dimethyl-2-[3-[4-(4-methylpiperazin-1-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCCOC1=CC=CC(C=2NC3=CC(C)=C(C)C=C3N=2)=C1 JYUNHIWFSACXRN-UHFFFAOYSA-N 0.000 claims 1
- DPLDJYIQOXPYEU-UHFFFAOYSA-N 5-chloro-2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-6-fluoro-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(Cl)=C(F)C=C2N1 DPLDJYIQOXPYEU-UHFFFAOYSA-N 0.000 claims 1
- DIUDUBNJSDXXFL-UHFFFAOYSA-N 5-chloro-2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-fluoro-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(Cl)=C(F)C=C2N1 DIUDUBNJSDXXFL-UHFFFAOYSA-N 0.000 claims 1
- RCFCAROGHBIRJE-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-(3-piperazin-1-ylpropoxy)phenyl]-6-fluoro-1h-benzimidazole Chemical compound N=1C=2C=C(Cl)C(F)=CC=2NC=1C(C=C1Cl)=CC=C1OCCCN1CCNCC1 RCFCAROGHBIRJE-UHFFFAOYSA-N 0.000 claims 1
- FSUQVEFSMOUIAJ-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC1=CC=C(C=2NC3=CC(C)=C(Cl)C=C3N=2)C=C1Cl FSUQVEFSMOUIAJ-UHFFFAOYSA-N 0.000 claims 1
- NNZBUWXJQQPPMT-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-fluoro-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1Cl NNZBUWXJQQPPMT-UHFFFAOYSA-N 0.000 claims 1
- NJEDSTVFVCYPMY-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(C)=C(Cl)C=C3N=2)C=C1Cl NJEDSTVFVCYPMY-UHFFFAOYSA-N 0.000 claims 1
- DMLVEFMJJRWHCV-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1F DMLVEFMJJRWHCV-UHFFFAOYSA-N 0.000 claims 1
- FWEZEGUGSRPQIY-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[3-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound COC1=CC(C=2NC3=CC(F)=C(Cl)C=C3N=2)=CC=C1OCCCN1CCN(C)CC1 FWEZEGUGSRPQIY-UHFFFAOYSA-N 0.000 claims 1
- ZGXXUVQKCZHGKT-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1C ZGXXUVQKCZHGKT-UHFFFAOYSA-N 0.000 claims 1
- NNVQDEHLJNCUEI-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1 NNVQDEHLJNCUEI-UHFFFAOYSA-N 0.000 claims 1
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| DE69330523D1 (de) * | 1992-08-21 | 2001-09-06 | Vrije Universiteit Brussel Bru | Immunoglobuline ohne leichte ketten |
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| KR20050033563A (ko) * | 2002-06-28 | 2005-04-12 | 센토코 인코포레이티드 | 포유동물 ｅｐｏ 모방 ｃｈ1 결실된 모방체, 조성물, 방법및 용도 |
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2004
- 2004-09-29 WO PCT/US2004/031858 patent/WO2005081687A2/en not_active Ceased
- 2004-09-29 US US10/953,613 patent/US20060127404A1/en not_active Abandoned
- 2004-09-29 JP JP2006534029A patent/JP4767857B2/ja not_active Expired - Fee Related
- 2004-09-29 EP EP04821516A patent/EP1687452A4/en not_active Withdrawn
- 2004-09-29 AU AU2004316266A patent/AU2004316266A1/en not_active Abandoned
- 2004-09-29 CN CNA2004800353031A patent/CN1890383A/zh active Pending
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